Citation:
Dai Hong, Chen Jia, Cao Xiongfei, Miao Wenke, Shi Yujun, Fang Jianxin, Ye Linyu, Zhong Sulin. Synthesis and Bioactivity of Novel Pyridine Phenyl Ethers Bearing N-heterocycles[J]. Chinese Journal of Organic Chemistry,
;2016, 36(2): 377-383.
doi:
10.6023/cjoc201510020
-
In order to find novel pyridine phenyl ether lead compounds, a series of novel pyridine phenyl ether derivatives containing N-heterocycles were prepared by the strategy of active substructure combination. Their structures were determined by 1H NMR, 13C NMR, IR and elemental analysis. Preliminary bioassay data displayed that some of the designed compounds exhibited good insecticidal activity. Additionally, some target compounds showed significant anti-tumor activities.
-
Keywords:
- N-heterocycle,
- pyridine phenyl ether,
- synthesis,
- bioactivity
-
-
-
[1]
[1] Sumida, M.; Niwata, S.; Fukami, H.; Tanaka, T.; Wakabayashi, K.; Boger, P. J. Agric. Food Chem. 1995, 43, 1929.
-
[2]
[2] Wang, M. H.; Yang, C. L.; Jiang, M. G. World Pestic. 2002, 24, 13 (in Chinese). (王鸣华, 杨春龙, 蒋木庚, 世界农药, 2002, 24, 13.)
-
[3]
[3] Ning, L. H.; Peng, H.; Tu, H. Y.; He, H. W. Chin. J. Pestic. Sci. 2004, 6, 74 (in Chinese). (宁丽红, 彭浩, 涂海洋, 贺红武, 农药学学报, 2004, 6, 74.)
-
[4]
[4] Freundlich, J. S.; Yu, M.; Lucumi, E.; Kuo, M.; Tsai, H. C.; Valderramos, J. C.; Karagyozov, L.; Jacobs, W. R. Jr.; Schiehser, G. A.; Fidock, D. A.; Jacobus, D. P.; Sacchettini, J. C. Bioorg. Med. Chem. Lett. 2006, 16, 2163.
-
[5]
[5] Liu, A. P.; Feng, Q. J.; Hu, C. H.; He, H. J.; Wang, T. J.; Liu, Y.; Lei, M. X.; Pang, H. L.; He, H. W. Chin. J. Org. Chem. 2008, 28, 531 (in Chinese). (柳爱平, 冯秋菊, 胡春华, 何海军, 王婷瑾, 刘洋, 雷满香, 庞怀林, 贺红武, 有机化学, 2008, 28, 531.)
-
[6]
[6] Kini, S. G.; Bhat, A. R.; Byrant, B.; Williamson, J. S.; Dayan, F. E. Eur. J. Med. Chem. 2009, 44, 492.
-
[7]
[7] Liu, J. C.; Cui, Z. P.; He, H. W. Chin. J. Org. Chem. 2012, 32, 1925 (in Chinese). (刘建超, 崔泽平, 贺红武, 有机化学, 2012, 32, 1925.)
-
[8]
[8] Anderson, J. W.; Sarantakis, D.; Terpinski, J.; Kumar, T. R. S.; Tsai, H. C.; Kuo, M.; Ager, A. L.; Jacobs, W. R. Jr.; Schiehser, G. A.; Ekins, S.; Sacchettini, J. C.; Jacobus, D. P.; Fidock, D. A.; Freundlich, J. S. Bioorg. Med. Chem. Lett. 2013, 23, 1022.
-
[9]
[9] Peng, H.; Gao, Y. J.; He, H. W. Chin. J. Org. Chem. 2013, 33, 1994 (in Chinese). (彭浩, 高玉焦, 贺红武, 有机化学, 2013, 33, 1994.)
-
[10]
[10] Zhang, Y. P.; Tan, W.; Yang, Y. S.; Sun, S. Q.; Guo, H. C. Chin. J. Org. Chem. 2015, 35, 1985 (in Chinese). (张应鹏, 谭伟, 杨云裳, 孙世琪, 郭慧琛, 有机化学, 2015, 35, 1985.)
-
[11]
[11] Kleemann, A.; Baltruschat, H. S.; Huelsen, T.; Thomas, S. S. EP 0723960, 1996 [Chem. Abstr. 1996, 125, 195679].
-
[12]
[12] Morimoto, K.; Ohnari, M.; Furusawa, H.; Terachi, T.; Nawamaki, T.; Ishikawa, K.; Nakahira, K.; Kawaguchi, C. WO 9606096, 1996 [Chem. Abstr. 1996, 125, 58524].
-
[13]
[13] Xu, Y. J.; Wang, Q. H.; Wu, J. Y.; Wu, H. B.; Ran, Z. J.; Mao, C. S.; Qin, Z. H. Chin. J. Pestic. Sci. 2007, 9, 189 (in Chinese). (徐彦军, 王庆海, 武菊英, 吴厚斌, 冉兆晋, 毛朝姝, 覃兆海, 农药学学报, 2007, 9, 189.)
-
[14]
[14] Ran, Z. J.; Ni, H. W.; Duan, H. X.; Li, N.; Dong, Y. H.; Fu, B.; Xiao, Y. M.; Qin, Z. H. Chin. J. Pestic. Sci. 2009, 11, 41 (in Chinese). (冉兆晋, 倪汉文, 段红霞, 李楠, 董燕红, 傅滨, 肖玉梅, 覃兆海, 农药学学报, 2009, 11, 41.)
-
[15]
[15] Li, R. J.; Bai, Y. H.; Shi, B.; Xiao, P. F. Chin. J. Pestic. 2007, 46, 305 (in Chinese). (李瑞军, 白延海, 史犇, 肖鹏飞, 农药, 2007, 46, 305.)
-
[16]
[16] Li, A. J.; Liu, B. S.; Yuan, B. G. Chin. J. Pestic. 2012, 51, 416 (in Chinese). (李爱军, 刘宝擅, 苑保国, 农药, 2012, 51, 416.)
-
[17]
[17] Ran, Z. J.; Yuan, H. Z.; Cao, A. C.; Qin, Z. H. Chin. J. Pestic. Sci. 2010, 12, 269 (in Chinese). (冉兆晋, 袁会珠, 曹坳程, 覃兆海, 农药学学报, 2010, 12, 269.)
-
[18]
[18] Ran, Z. J.; Yuan, H. Z.; Cao, A. C.; Qin, Z. H. Chin. J. Pestic. Sci. 2010, 12, 458 (in Chinese). (冉兆晋, 袁会珠, 曹坳程, 覃兆海, 农药学学报, 2010, 12, 458.)
-
[19]
[19] Zhang, A. G.; Kayser, H.; Maienfisch, P.; Casida, J. E. J. Neurochem. 2000, 75, 1294.
-
[20]
[20] Zhang, G. S.; Hou, G. X. Pestic. Sci. Admin. 2004, 25, 22 (in Chinese). (张国生, 侯广新, 农药科学与管理, 2004, 25, 22.)
-
[21]
[21] Dai, B. J. World Pestic. 2005, 27, 46 (in Chinese). (戴宝江, 世界农药, 2005, 27, 46.)
-
[22]
[22] Shao, X. S.; Tian, Z. Z.; Li, Z.; Xu, X. Y.; Huang, Q. C.; Qian, X. H. Chin. J. Pestic. Sci.. 2008, 10, 117 (in Chinese). (邵旭升, 田忠贞, 李忠, 徐晓勇, 黄青春, 钱旭红, 农药学学报, 2008, 10, 117.)
-
[23]
[23] Yokota, T.; Mikata, K.; Nagasaki, H.; Ohta, K. J. Agric. Food Chem. 2003, 51, 7066.
-
[24]
[24] Kagabu, S.; Ishihara, R.; Hieda, Y.; Nishimura, K.; Naruse, Y. J. Agric. Food Chem. 2007, 55, 812.
-
[25]
[25] Bouillot, A. M. J.; Dodic, N.; Gellibet, F. J.; Mirguet, O. WO 2009071504, 2009 [Chem. Abstr. 2009, 151, 33581].
-
[26]
[26] Wang, T. T.; Bing, G. F.; Zhang, X.; Qin, Z. F.; Yu, H. B.; Qin, X.; Dai, H.; Miao, W. K.; Wu, S. S.; Fang, J. X. Bioorg. Med. Chem. Lett. 2010, 20, 3348.
-
[27]
[27] Wu, S. S.; Miao, W. K.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2015, 35, 1484 (in Chinese). (吴珊珊, 苗文科, 王婷婷, 方建新, 有机化学, 2015, 35, 1484.)
-
[28]
[28] Ma, Y. M.S. Thesis, Nankai University, Tianjin, 2009 (in Chinese). (马云, 硕士论文, 南开大学, 天津, 2009.)
-
[29]
[29] Liu, J. C.; Liu, Y. J.; He, H. W. Chin. J. Org. Chem. 2015, 35, 462 (in Chinese). (刘建超, 刘勇军, 贺红武, 有机化学, 2015, 35, 462.)
-
[1]
-
-
-
[1]
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
-
[2]
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
-
[3]
Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two LnⅢ3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
-
[4]
Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
-
[5]
Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
-
[6]
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
-
[7]
Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
-
[8]
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
-
[9]
Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
-
[10]
Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
-
[11]
Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
-
[12]
Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
-
[13]
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
-
[14]
Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
-
[15]
Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
-
[16]
Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
-
[17]
Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
-
[18]
Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
-
[19]
Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
-
[20]
Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
-
[1]
Metrics
- PDF Downloads(1)
- Abstract views(972)
- HTML views(88)